Anal Sex – Laying the Groundwork

In the overview section of this topic, I described an example scenario where Roger and Alison have been a happy, wedded couple for about five years. Over time, however, their sex life has gotten a little stale. Roger would like to liven things up a little, and has confided in his wife that he’s curious about anal sex and would really like to try it with her. Alison however, hasn’t felt quite so enthusiastic, and has been rather emphatic about her answer. “No!” about sums it up.

We’ve talked a little about reasons why Alison might feel this way, and they include bad information about or perceptions of anal sex, a feeling that it is “dirty”, and probably even a little bit of fear. (It might hurt!) In this posting, I’m going to talk about ways to start gradually helping Alison overcome some of these feelings, so that she comes to see her rear entry as a potential source of pleasure and an erogenous zone.

Wives or girlfriends, if you’re reading the following, that’s fine—there is good info here for you to learn about. But I want to let you know that the rest of this post is really targeted towards the husbands and boyfriends.

Okay, guys, first notice that we’re starting with something of a worst case scenario. Roger’s already asked Alison if she’d be willing to having him in her ass, and Alison has said “No!” In an ideal situation, Roger would have read this series of posts before he broached the subject, and he wouldn’t be in the situation of having to overcome an explicit “no”. It’s better to start taking steps down the path laid out in this series without ever asking about your intended final destination–it will make things a little easier. If your wife has never told you “no”, it will be that much easier to tell you “yes, yes!” when the time eventually comes. So if you haven’t already asked, don’t. On the other hand, if you already have asked, don’t worry–you, like Roger, can still be successful.

“But wait a minute!” you say. “What if my wife would say yes right off the bat? Then I could skip all the rigmarole you’re about to write about and get straight to the good stuff!”

Well, maybe. If you’re confident that your wife will be open to the idea, then you’ll probably be okay. But I’d still recommend you read on if you’re new to anal sex. There are several things you should do even if your wife is eager to give it a try. It’s important to make sure she has a positive experience her first time, so that she is willing to come back for another round at a later date. Many women have tried anal sex exactly once…and had a bad experience, and never given it another chance. You want to make sure that doesn’t happen to your wife…and you.

Let’s return to poor Roger. He has to convince Alison that she really does want to let him in her ass, in spite of the fact that she’s said she will not do so.

The first thing that Roger needs to keep in mind is that he’s not going to build Rome in a day. Roger needs to look for steps he can take towards his ultimate goal, steps that Alison will not be afraid of or object to. The idea here is for Roger to make incremental progress towards his destination, because trying to get there all at once will sink him like the Titanic.

So what kinds of steps can Roger take? Well, the first, best, and most-likely-to-succeed step is to use his tongue.

“Whoa!” you say. “I am not going there!” To which I answer, “How badly do you want your wife’s ass?”

Listen, if you’re any good in bed, you already go down on your wife or girlfriend. All you need to do is move your tongue a couple inches south and you’re there. Or, start with your wife lying on her belly and kiss lightly over the crease between her leg and her butt cheek (a highly erogenous area for many women), then move inwards and upwards from there. If you’re worried about cleanliness, then pick an occasion when she has just come out of the bath or shower and you know she’s squeaky clean.

I’d be very surprised if she made any objection, because it’s going to feel very good to her. Oh, she might be a bit surprised, but be gentle and unafraid. Explore with your tongue, and I bet in about a minute she’ll be gasping with excitement, and in two minutes she’ll be hot enough to singe the bed sheets.

Once you’ve done this, stop! Don’t go any further this session! Go back to your normal sexual routine, and act like nothing’s changed. Chances are good you’ll both have lots of fun because your wife or girlfriend is so aroused! If she asks about what you did afterwards, act like it was nothing surprising. “I just wanted to make you feel good,” is the line to take.

Then, for at least a couple weeks, don’t go there again. Have standard, garden variety sex, and leave her rear end strictly alone. Let anticipation work its magic–time is on your side.

So what happens when Roger tries this approach? “Roger..what?” Oh my God!” Alison gasps as Roger’s tongue finds its target. “OH…oh…” After a couple seconds Alison relaxes and let’s Roger’s tongue have free rein. A few minutes later they change positions, and Alison reaches an extraordinarly strong orgasm, clutching Roger fiercely as she climaxes.

Roger has accomplished his goal for today–he’s helped Alison to realize that her ass can be an erogenous zone, and quite a powerful one. His next goal is to give Alison time to internalize that realization, come to accept it, and decide that she wants to experience the sensation again. After a couple weeks he can move on to the next step, penetration, but for now, he needs to wait.

If you truly cannot bring yourself to follow this step, you can try skipping it and moving directly to penetration, but I warn you that your chances of success will diminish greatly. With that understanding, feel free to make your own decision…

6 Comments (and one trackback)

Suppose that Roger has already indicated to his wife that he’d like oral on her to include ‘around the back’, and she’s totally ruled it out on the grounds that it’s not hygienic? His protestations that it’s he who’s doing it to her, rather than the other way around, and that anyway sex doesn’t necessarily have to be hygienic have had no effect.

I’m going to guess that you already took the approach of asking permission. My recommendation going forward is to not ask, but instead, simply do. If your aren’t fighting against an explicit “no”, it’s much easier. However, we are where we are, right?

I have two possible courses of action for you. The first is to move on to the next step–penetration using your finger–anyway. It’s not clear to me from your comment whether this has already been ruled out of bounds or not. If it hasn’t, wait until “Alison” is very hot, probably due to vanilla oral sex, and then moisten your finger and insert it, ideally at the same time that you’re going down on her. She may decide right then and there that she’s not all that worried about how hygienic anal sex is after all. As an added precaution, consider waiting for an opportunity in which Alison has just come out of the bath or shower, so mentally she “feels” clean.

No guarantees that this approach will work–Alison may put the brakes on almost before you get started. But there’s a good chance it will succeed.

The second option is a much longer road. Consider pursuing an entirely different tack, and coming back to anal sex later. Consider adding some light Domination and submission to your bedroom activities. If Alison learns that she enjoys it when you Dominate her, she will be much less inclined to balk at anal sex when your circle back around to trying it. For information on how to tackle exploring D/s, take a look at my series of posts on introducing bondage to your bedroom.

If having your tongue in her ass will squick her out, how about making an improvised dental dam made from a rubber surgical glove? She’ll still feel your tongue in her ass, but won’t have to deal with your ass-breath afterwards. Hint: ass-breath=not-sexy.
Cut the four fingers off the glove, leaving the thumb on, then cut up the pinkie side so it will lay flat when opened. Lay that across her butt, thumb part on her anus, then insert tongue into the thumb-sleeve and gently lick and probe her ass. Don’t forget to put lubrication on the butt-side of the glove. Put flavored lube on the tongue side, if you have it, and viola, a potential ass-breath situation turns to a clean, good-tasting strawberry kiss afterwards. No mouthwash required. It should still be a taboo act for her, but not gross in the least.

Guys and gals, your woman wants you to see her as sexy. How is she supposed to feel sexy when she’s worried about you tasting her shit and possibly getting sick?

It would seem important to let her know you are using a barrier just before you lick her ass. I’d think that would let her relax and enjoy it more, since she’ll know there’s no chance you’ll be tasting her shit.

Also, medically speaking, there’s much less chance of you getting sick from E. coli around and/or inside her anus if you use a barrier.

Folks, this just makes sense. Safe sex makes sense.

If she enjoys being tied up, then this process will be much easier. Take control of her and warm her up with whatever gets her motor going; cunnilingus, manual stimulation, vibrator—whatever your woman enjoys. Get her close to orgasm before you tongue-glove her ass. As you’re working her anus, stimulate her clit with your fingers or vibrator. Try your damnedest to give her an orgasm with your tongue in her ass. This is your best shot at showing her that anal stimulation can enhance or even cause her to orgasm. Do your part right and she’ll have nothing to object to, from a hygiene point of view.

I agree with the post. Don’t go there again after this for a while. Let her internalize the experience. Keeping it clean in the way I suggested might even lead to her asking for it again before those few weeks are up. Why leave her to struggle with the good sensations vs the bad hygiene if you don’t have to?

Bill, honestly-speaking, I don’t know that there is such a thing as “ass-breath”. This is more of a perception issue, I think, than a real problem. Nonetheless, I hear your point about getting sick and the importance of cleanliness. If that’s a concern, then the route you prescribe might be an option. My own medically-uneducated opinion, however, is that with one’s spouse, one already shares sufficient bodily fluids and germs that it’s kind of a moot point. In addition, the situation this post describes, in which things may be balanced on a razor’s edge between desire and fear/inhibition, does not lend itself to improvised tools that may increase awkwardness. I’m personally far more of an advocate of simply using one’s tongue, and I think success rates will be better that way. However, that’s just me…others (such as yourself) may feel differently.

Excellent question, Darren. I’m wondering whether this is actually a trust issue more than anything else. Sometimes, even in a relationship, one partner is afraid to explore their kinky desires because they’re not yet ready to expose themselves so fully to their partner. Do you think that could be the case here? Even if you’re not sure, I’d highly recommend the strategies of taking baby steps and planting seeds and then letting them grow for awhile before you come back to them. Patience will take you a long way sometimes. If you want more info on these ideas, reply back and I’ll point you to some posts I wrote about them.

To directly answer your question, I’d suggest a couple different possibilities. One option would be to use her own desires as a lever to help you overcome the issue. In other words, get her so turned on before you start with your tongue that she’s past worrying about whether it’s weird and focused only on how it feels. However, this will only work if you succeed in raising her arousal to very high levels, and that is partially dependent on the trust I mentioned above being in place.

A different option would be to skip using your tongue. I assume that you’ve already used your finger in your partner’s rear-entry, correct? If the tongue is an issue, consider buying a small anal plug and inserting that prior to moving on to vaginal intercourse. This will help prepare her for the idea of having you enter her ass (and she may very well find that she likes anal plugs!).

One other option would be to forego pursuing anal sex for the moment and travel in a different direction, though continuing to use your finger in her rear end when you give her head so that you don’t lose the progress you’ve made so far. You can come back to the idea of using your tongue in a couple months, after she’s had more time to internalize the idea. What direction should you go in the meantime? That’s up to you, but if you have an interest in bondage and can successfully introduce it into your bedroom, it will lead down a path that will eventually make it easier for you to circle back to anal sex.

Hope these ideas help, and if you have more questions, let me know. Best of luck!

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